Insecticides



Patented June 26, 1945 UNITED STATES PATENT OFFICE; T I 'zsrazes v v Theodore W. Evans, Oakland, and,

Williams, Berkeley, Calif assiano,

Paul H. to'shell Development Company, San Francisco, Caliih, a corporation of Delaware No Drawing. Application June so, 1942; 9,168

SerialNo.

. aclaims. ((1167-24) disti lli'ngwithout decomposition at 174 C.to m

This invention deals with a new insecticide oi Brest utility, and is particularly .concemed with toxic substances suitable for use in household insecticides and de-lousing powders. Among the known and most useful toxicants for such purposes at present are pyrethrum and rotenone.

I These are both derived from plants grown in foreign countries and are therefore ex nsive and not always obtainable in desired quantities.

It is an object of the present invention to provide. an insecticide whichcan be readily manuiactured from readily available domestic, inexpensive materials. It is a further object of this invention to provide a very toxic, moderately iast actinglnsecticide which is littleii at all toxic to loan and other warm-blooded animals. Another object is to provide a synthetic toxicant which is stable toward sunlight and which is compatible with plant toxics. Other and iurthe'robiects will be apparent from reading the specification.

acting di-allyl amines with aliphatic carboxylic' acids may be utilised as insecticides to accomplish one or more of the foregoing objects.

The di-allyl amines whichare. used to Produce the di-allyl amides or the invention are preferably C. at about 1 mm. pressure was obtained.

The di-allyl amide so obtained was utilised as a toxic in a mineral oil iiy spray both with and without the addition of 'pyrethrum. Itskilling Power proved to be more than twice that of. the

most efiective amidedescribed in the literature.

A few drops of a solution of N,N-dialiyhmdec-' yleneamide in odorless base. kerosene was placed -on filter paper and exposed to strong simlight and air. The liquid evaporated leaving substantially no stain behind. This property is important in household insecticides and the like where absence oistainishighlydesirable.

ways. For use in household insecticides the comsolved in a plant spray oil and emulsified in water.

unsubstituted di-allyl amines. However, one or both of the allyl groups may contain beta alkyl 4 substitution. or 1 to 4 carbon atoms, such as in dimethallyl amide of 'undecylenic acid,

The aliphatic carboxylic acids which are employed to produce the di-alL'vl amides should con-' tain about 9 to 18 carbon atoms, although acids containing a greater and lesser number of carbon:

atoms are included within the scope of the invention. The hydrocarbon radical of the acid may be saturated, unsaturated, straight, branched, or a mixed-chain radical. The amides produced by reacting the di-allyl amines with undecylenic acid have proved unusually effective.

An example of the production of a suitable amide follows:

Toan ice-cooled benzene solution containing 48.5 grams (.5 mols) of di-allyl amine was added grams (.25 mole) of undecylenic acid chloride,

Prepared by reacting undecylenic acid and phos-' The temperature was.

phorus pentachloride. maintained below 10 C. during the addition of the acid chloride. and the mixture. was shaken and cooled for ,5 hour aiter the final addition.

The product mixture was then washed with dilute hydrochloric acid and with water. The remaining bensenesoiutionwas then distilledand64 grams. or 97% yield, based on acid chloride, of product The insecticide or the'instant invention may be applied to plants and animals in a variety of p unds may e dissolved in a light hydrocarbon oil such as'kero'sene or kerosenedistillate with v '20 It has been found that amides produced by reor without the addition of other insecticides and. am 'Ol'dindl'fl! from about 396-3555 0! the toxicants are used in such sprays.

For use on plants the acid amides may be disto produce sprayableemulsions. The common emulsifying agents such as glycerol mono-oleate. suliated and sulionated iatty and mineral oils.

soapsand the like, may be used in combinationv with such sprays. In the same manner, the acid amides themselves without the addition or oil may be' emulsified and used as plant spray insecticides.

The amides or our invention may also be adsorbed on finely divided materials such as wood fiber, talc clay, sulfur or carbon black and beused as dusting insecticides or de-louslng agents.

We claim as our invention: 1. .An insecticidal composition comprising a carrier and a di -allyl amide of an aliphatic carboxylic acid of 9 to 18 carbon atoms.

2. An insecticidal composition comprising a carrier and a di-allyl amide oi undecylenic acid. 3. An insecticidal composition comprising a carrier and a di-allyl amide of 'an aliphatic carboxylic acid-019 to 18 carbon atoms, said compound being further characterized by beta alkyl rethrum and a di-allyl amide of an aliphatic car-. boxylic acid of 9 to 18 carbon atoms.

7. A plant spray insecticide comprising a plant spray mineral oil, an emulsifying agent, and a di-allyl amide of an aliphatic carboxylic acid of 9 to 18 carbon atoms. 7

8. A dust insecticidal composition comprising a finely divided absorptive substance and a diwhich comprises a di-allyl amide of an aliphatic 5 carboxylic acid of9 to 18 carbon atoms.

THEODORE w. iz'vms. PAUL H. wn-mms. 

